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The title compound, C9H18NO2+·NO3, was prepared by an anion exchange from Cl to NO3 by adding excess NaNO3 to an aqueous solution of (1S,3R)-3-amino-2,2,3-trimethyl­cyclo­pentane-1-carboxylic acid hydro­chloride. O—H...O and N—H...O hydrogen-bond inter­actions are observed, through which each nitrate anion links three adjacent cations, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025809/ez2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025809/ez2077Isup2.hkl
Contains datablock I

CCDC reference: 290195

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.059
  • wR factor = 0.130
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.10 From the CIF: _reflns_number_total 1657 Count of symmetry unique reflns 1688 Completeness (_total/calc) 98.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(1S,3R)-1-Carboxy-2,2,3-trimethylcyclopentane-1-ammonium nitrate top
Crystal data top
C9H18NO2+·NO3F(000) = 504
Mr = 234.25Dx = 1.302 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 822 reflections
a = 7.0696 (19) Åθ = 3.3–21.0°
b = 12.473 (3) ŵ = 0.11 mm1
c = 13.555 (4) ÅT = 291 K
V = 1195.3 (6) Å3Plate, colourless
Z = 40.50 × 0.40 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1657 independent reflections
Radiation source: fine-focus sealed tube1256 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 28.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.951, Tmax = 0.966k = 1613
7286 measured reflectionsl = 1517
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0633P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1657 reflectionsΔρmax = 0.25 e Å3
145 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods
Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. Main FT–IR (KBr plates, cm-1): 3350–2850 (b, s), 1727 (m), 1695 (s), 1528 (m), 1500 (w), 1416 (m), 1384 (versus), 1315 (s), 1236 (m), 1206 (m) and 1152 (w). ESI-MS: m/z 172.1 [C9H17NO2H]+ (100%)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7780 (5)0.8112 (2)0.1218 (2)0.0459 (7)
H1A0.86120.82200.06480.055*
C20.8917 (4)0.8369 (2)0.2179 (2)0.0418 (7)
C30.7419 (4)0.8922 (2)0.2844 (2)0.0373 (6)
C40.6235 (5)0.9575 (3)0.2130 (2)0.0513 (8)
H4A0.49680.96770.23880.062*
H4B0.68041.02730.20220.062*
C50.6172 (6)0.8948 (3)0.1177 (2)0.0654 (11)
H5A0.63500.94240.06180.079*
H5B0.49590.85920.11070.079*
C60.7017 (5)0.6995 (2)0.1185 (2)0.0462 (8)
C70.8165 (6)0.9572 (3)0.3704 (2)0.0593 (9)
H7A0.71240.98790.40600.089*
H7B0.89681.01340.34610.089*
H7C0.88770.91140.41360.089*
C80.9861 (6)0.7406 (3)0.2650 (3)0.0650 (10)
H8A1.04580.76200.32550.097*
H8B1.07950.71210.22080.097*
H8C0.89270.68670.27860.097*
C91.0451 (6)0.9177 (3)0.1902 (3)0.0726 (12)
H9A1.11260.93900.24850.109*
H9B0.98770.97960.16050.109*
H9C1.13130.88540.14430.109*
N10.6150 (4)0.80843 (19)0.32904 (16)0.0445 (6)
H1B0.51450.84000.35590.067*
H1C0.67810.77260.37530.067*
H1D0.57730.76310.28230.067*
N20.2273 (4)0.1248 (2)0.99836 (17)0.0459 (6)
O10.5708 (4)0.6693 (2)0.16836 (19)0.0771 (9)
O20.7874 (4)0.63802 (18)0.05624 (16)0.0652 (7)
H2A0.74380.57900.06510.098*
O30.3231 (4)0.08986 (19)1.06495 (16)0.0643 (7)
O40.1672 (4)0.06448 (18)0.93074 (16)0.0626 (7)
O50.1874 (5)0.22022 (18)0.99345 (18)0.0761 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0573 (19)0.0462 (17)0.0342 (13)0.0035 (15)0.0112 (15)0.0009 (12)
C20.0392 (16)0.0427 (15)0.0435 (15)0.0007 (14)0.0048 (14)0.0042 (13)
C30.0401 (15)0.0344 (14)0.0373 (12)0.0005 (13)0.0015 (12)0.0015 (11)
C40.063 (2)0.0438 (16)0.0471 (16)0.0108 (16)0.0009 (17)0.0043 (14)
C50.088 (3)0.062 (2)0.0467 (17)0.015 (2)0.015 (2)0.0025 (16)
C60.055 (2)0.0498 (18)0.0340 (14)0.0061 (16)0.0036 (16)0.0066 (13)
C70.069 (2)0.0583 (19)0.0504 (17)0.0030 (18)0.0022 (19)0.0146 (15)
C80.058 (2)0.071 (2)0.066 (2)0.024 (2)0.0036 (19)0.007 (2)
C90.054 (2)0.079 (3)0.085 (3)0.022 (2)0.020 (2)0.017 (2)
N10.0507 (15)0.0479 (14)0.0350 (12)0.0042 (13)0.0062 (12)0.0004 (11)
N20.0493 (15)0.0445 (15)0.0439 (13)0.0038 (13)0.0007 (14)0.0073 (12)
O10.090 (2)0.0665 (15)0.0747 (16)0.0313 (15)0.0360 (16)0.0288 (14)
O20.0814 (18)0.0495 (12)0.0647 (14)0.0117 (12)0.0270 (14)0.0201 (11)
O30.0740 (17)0.0661 (14)0.0530 (12)0.0047 (13)0.0223 (14)0.0008 (11)
O40.0780 (17)0.0521 (13)0.0577 (13)0.0111 (12)0.0260 (13)0.0216 (11)
O50.102 (2)0.0509 (14)0.0751 (16)0.0147 (15)0.0264 (17)0.0136 (12)
Geometric parameters (Å, º) top
C1—C61.495 (4)C7—H7A0.9600
C1—C51.543 (5)C7—H7B0.9600
C1—C21.564 (4)C7—H7C0.9600
C1—H1A0.9800C8—H8A0.9600
C2—C81.515 (4)C8—H8B0.9600
C2—C91.528 (5)C8—H8C0.9600
C2—C31.552 (4)C9—H9A0.9600
C3—N11.504 (4)C9—H9B0.9600
C3—C71.515 (4)C9—H9C0.9600
C3—C41.517 (4)N1—H1B0.8900
C4—C51.511 (5)N1—H1C0.8900
C4—H4A0.9700N1—H1D0.8900
C4—H4B0.9700N2—O31.210 (3)
C5—H5A0.9700N2—O51.225 (3)
C5—H5B0.9700N2—O41.259 (3)
C6—O11.206 (4)O2—H2A0.8068
C6—O21.291 (3)
C6—C1—C5111.3 (3)O1—C6—C1123.4 (3)
C6—C1—C2113.7 (2)O2—C6—C1113.8 (3)
C5—C1—C2105.7 (2)C3—C7—H7A109.5
C6—C1—H1A108.7C3—C7—H7B109.5
C5—C1—H1A108.7H7A—C7—H7B109.5
C2—C1—H1A108.7C3—C7—H7C109.5
C8—C2—C9108.3 (3)H7A—C7—H7C109.5
C8—C2—C3114.1 (2)H7B—C7—H7C109.5
C9—C2—C3109.5 (3)C2—C8—H8A109.5
C8—C2—C1114.5 (3)C2—C8—H8B109.5
C9—C2—C1107.2 (3)H8A—C8—H8B109.5
C3—C2—C1103.0 (2)C2—C8—H8C109.5
N1—C3—C7105.7 (2)H8A—C8—H8C109.5
N1—C3—C4107.5 (3)H8B—C8—H8C109.5
C7—C3—C4113.3 (2)C2—C9—H9A109.5
N1—C3—C2109.4 (2)C2—C9—H9B109.5
C7—C3—C2116.5 (3)H9A—C9—H9B109.5
C4—C3—C2104.1 (2)C2—C9—H9C109.5
C5—C4—C3106.5 (2)H9A—C9—H9C109.5
C5—C4—H4A110.4H9B—C9—H9C109.5
C3—C4—H4A110.4C3—N1—H1B109.5
C5—C4—H4B110.4C3—N1—H1C109.5
C3—C4—H4B110.4H1B—N1—H1C109.5
H4A—C4—H4B108.6C3—N1—H1D109.5
C4—C5—C1107.3 (3)H1B—N1—H1D109.5
C4—C5—H5A110.3H1C—N1—H1D109.5
C1—C5—H5A110.3O3—N2—O5121.3 (3)
C4—C5—H5B110.3O3—N2—O4121.1 (3)
C1—C5—H5B110.3O5—N2—O4117.6 (3)
H5A—C5—H5B108.5C6—O2—H2A105.4
O1—C6—O2122.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.892.022.897 (3)166
N1—H1B···O5i0.892.473.109 (4)130
N1—H1C···O3ii0.892.423.113 (3)135
N1—H1C···O5ii0.892.122.992 (4)166
N1—H1D···O10.891.942.802 (3)163
O2—H2A···O4iii0.811.872.671 (3)171
C5—H5B···O10.972.552.914 (5)102
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2; (iii) x+1/2, y+1/2, z+1.
 

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